US3471567A - Preparation of glyoxal - Google Patents

Preparation of glyoxal Download PDF

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Publication number
US3471567A
US3471567A US665229A US3471567DA US3471567A US 3471567 A US3471567 A US 3471567A US 665229 A US665229 A US 665229A US 3471567D A US3471567D A US 3471567DA US 3471567 A US3471567 A US 3471567A
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United States
Prior art keywords
parts
palladium
ethylene
glyoxal
reaction
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Expired - Lifetime
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US665229A
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English (en)
Inventor
George Gourlay
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties

Definitions

  • the reaction is preferably carried out using technically pure ethylene.
  • a mixture of ethylene with other gases for example ethylene-ethane mixtures, can be used although it is preferred that other olefines should not be present in large amounts, as the purity of the product glyoxal is adversely affected by their presence.
  • EXAMPLE 8 2.44 parts of palladous nitrate were added to 180 parts of a 20% aqueous solution of nitric acid at 35 C. and ethylene was passed through the mixture at a rate of 25 parts per hour as described in Example 1. 1.1 parts of lithium nitrate trihydrate and 0.62 parts of sodium nitrate were then added and the palladium which had been precipitated dissolved rapidly. After minutes reaction was complete. 6.4 parts of ethylene had been absorbed and the reaction mixture contained 11.15 parts of glyoxal (84% of theoretical). Most of the palladium precipitated from the solution and was filtered off.
  • EXAMPLE 10 1.93 parts of palladous sulphate were added to 180 parts of a 20% aqueous solution of nitric acid at 35 C. and ethylene was passed through the mixture at a rate of 25 parts per hour as described in Example 1. 0.38 parts of lithium chloride and 0.62 parts of sodium nitrite were then added and the palladium which had been precipitated dissolved rapidly. After 5 hours the reaction was complete. 6.05 parts of ethylene had been absorbed and the reaction mixture contained 9.8 parts of glyoxal (78% of theoretical). Most of the palladium precipitated from the solution and was filtered off. The glyoxal solution was purified by passage through a bed of active carbon, and through cationic and anionic resin exchange columns as described in Example 1, and finally concentrated by distillation under reduced pressure.
  • EXAMPLE 11 1.6 parts of palladous chloride were added to 180 parts of a 20% aqueous solution of nitric acid at 35 C. and
  • ethylene was passed through the mixture at a rate of 25 parts per hour as described in Example 1.
  • 1.1 parts of lithium nitrate and 0.62 parts of sodium nitrite were then added and the palladium which had been precipitated dissolved rapidly.
  • the reaction was complete.
  • 6.0 parts of ethylene had been absorbed and the reaction mixture contained 11.35 parts of glyoxal (92% of theoretical).
  • the filtrate was neutralised to pH 7 by the addition of calcium carbonate, and the resultant precipitate of calcium salts of organic acids and further palladium was filtered off before final purification of the glyoxal solution by ion-exchange resins and concentration by distillation under reduced pressure, as described in Example 1.
  • EXAMPLE 12 1.6 parts of palladous chloride were added to 180 parts of a 20% aqueous solution of nitric acid at 35 C. and ethylene was passed through the mixture at a rate of 25 parts per hour as described in Example 1. 0 .33 parts of lithium carbonate and 0.62 parts sodium nitrite were then added, and the palladium which had been precipitated dissolved rapidly. After 6 /2 hours the reaction was stopped. 6.2 parts of ethylene had been absorbed and the reaction mixture contained 11.1 parts (87% of theoretical) of glyoxal. The solution was purified by addition of calcium carbonate and ion-exchange treatment as described in Example 11.
  • a process for the preparation of glyoxal wherein ethylene is oxidised by nitric acid in aqueous medium in presence of a catalytic mixture of a water-soluble lithium salt and at least 0.01% by weight of the reaction mixture of a palladium metal or a palladium salt, the concentration of nitric acid being at least by weight of the reaction mixture.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US665229A 1966-09-22 1967-09-05 Preparation of glyoxal Expired - Lifetime US3471567A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB42370/66A GB1130760A (en) 1966-09-22 1966-09-22 Preparation of glyoxal

Publications (1)

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US3471567A true US3471567A (en) 1969-10-07

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ID=10424125

Family Applications (1)

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US665229A Expired - Lifetime US3471567A (en) 1966-09-22 1967-09-05 Preparation of glyoxal

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US (1) US3471567A (enrdf_load_html_response)
FR (1) FR1550221A (enrdf_load_html_response)
GB (1) GB1130760A (enrdf_load_html_response)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3655363A (en) * 1970-10-23 1972-04-11 Kuraray Co Method of recovering palladium
US3961943A (en) * 1975-04-18 1976-06-08 The Dow Chemical Company Process for recovering palladium

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3900379A1 (de) * 1989-01-09 1990-07-12 Basf Ag Verfahren zur reinigung waessriger glyoxalloesungen
FR3056658B1 (fr) 2016-09-26 2018-12-07 Valeo Embrayages Mecanisme de filtrage entre deux organes tournants

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3288845A (en) * 1963-06-18 1966-11-29 Union Oil Co Method of preparing unsaturated esters by oxidation of olefins
US3333004A (en) * 1962-07-18 1967-07-25 Basf Ag Production of glyoxal

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3333004A (en) * 1962-07-18 1967-07-25 Basf Ag Production of glyoxal
US3288845A (en) * 1963-06-18 1966-11-29 Union Oil Co Method of preparing unsaturated esters by oxidation of olefins

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3655363A (en) * 1970-10-23 1972-04-11 Kuraray Co Method of recovering palladium
US3961943A (en) * 1975-04-18 1976-06-08 The Dow Chemical Company Process for recovering palladium

Also Published As

Publication number Publication date
DE1668273B1 (de) 1971-06-09
FR1550221A (enrdf_load_html_response) 1968-12-20
GB1130760A (en) 1968-10-16

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